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Method for preparing sermorelin acetate

A technology for the synthesis of acetic acid and peptides, applied in the preparation methods of peptides, chemical instruments and methods, peptides, etc., can solve the problems of increasing the difficulty of purification, increasing the cost of the final product, etc., to achieve the synergy of catalytic condensation performance, and enhance the promotion of non-specific immunity. Functional ability, high application value effect

Active Publication Date: 2022-03-18
ZHEJIANG PEPTITES BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As the length of the peptide chain increases, the type and content of impurities increase, and the structure of the impurities is very similar to the final product, which will greatly increase the difficulty of purification and increase the cost of the final product

Method used

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  • Method for preparing sermorelin acetate
  • Method for preparing sermorelin acetate
  • Method for preparing sermorelin acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Preparation of ionic liquid:

[0067] Add imidazole and NaH into THF, stir at 0°C for 45 min, return to room temperature, add 1-bromooctane, and stir for 24 h; extract with THF and purify by thin-layer silica gel column to obtain product A; among them, imidazole The molar ratio of NaH to NaH is 1:1; the solid-liquid ratio of imidazole to THF is 0.35 g / mL; the molar ratio of 1-bromooctane to imidazole is 1.1:1;

[0068] Dissolve 1,6-dibromohexane in acetonitrile at a concentration of 1.2 g / mL, heat to reflux, and slowly add the acetonitrile solution of product A (the molar ratio of 1,6-dibromohexane is 1:15.5) dropwise (Concentration: 0.16 g / mL), the system was reacted at 92°C for 24 h; the solvent was distilled off under reduced pressure, and washed 4 times with anhydrous ether to obtain product B;

[0069] Get product B and 4-(azidine-3-yl) piperazine-1-carboxylate tert-butyl ester (the molar ratio of both is 1: 1.3) and potassium carbonate is added (the molar ratio w...

Embodiment 2

[0098] The preparation of the ionic liquid was the same as in Example 1.

[0099] The difference between a method for preparing sermorelin acetate and Example 1 is that HBTU is used instead of HOBt in step 6;

[0100] NMM is used instead of DIC.

Embodiment 3

[0102] The preparation of the ionic liquid was the same as in Example 1.

[0103] The difference between a method for preparing sermorelin acetate and Example 1 is:

[0104]In step 2, the mol ratio of ionic liquid and DMAP is 1: 2;

[0105] In step 6, the molar ratio of ionic liquid to HOBt is 1:2.

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Abstract

The invention discloses a method for preparing sermorelin acetate, and relates to the technical field of polypeptide synthesis, and the sermorelin acetate is prepared by a polypeptide solid-phase synthesis method; wherein a condensing agent used in the synthesis process comprises ionic liquid; the ionic liquid is salt composed of anions and cations; the anion comprises [NTf2] <->; the cation structure at least comprises imidazole, aza-pyridine, alkyl and ester group. The purity and the yield of the sermorelin acetate prepared by the method provided by the invention are obviously increased; and the stability and half-life period of the product are obviously increased, and the immunocompetence is effectively improved.

Description

technical field [0001] The invention belongs to the technical field of polypeptide synthesis, and in particular relates to a method for preparing sermorelin acetate. Background technique [0002] Sermorelin acetate is a synthetic growth hormone releasing hormone with 29 amino acids, which is the amino-terminal fragment of endogenous growth hormone releasing hormone (GHRH), and has significant growth-regulating effects. The traditional synthetic method of sermorelin acetate is chemical method. Chemical synthesis reactions are highly dependent on peptide sequence, and method development and analysis become critical as peptide complexity increases. In general, chemical peptide synthesis includes several main steps of protection, activation, condensation and deprotection. The main problems in the chemical synthesis route include low solubility and racemization of the fragments. As the length of the peptide chain increases, the types and contents of impurities increase, and th...

Claims

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Application Information

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IPC IPC(8): C07K14/60C07K1/06C07K1/04C07K1/14
CPCC07K14/60
Inventor 张启鹏魏祝宇潘海良汪岳斌
Owner ZHEJIANG PEPTITES BIOTECH CO LTD
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